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Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis.
Siebert, David C B Sommer, Roman Pogorevc, Domen Hoffmann, Michael Wenzel, Silke C Müller, Rolf
Siebert, David C B
Sommer, Roman
Pogorevc, Domen
Hoffmann, Michael
Wenzel, Silke C
Müller, Rolf
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2019-01-01
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Abstract
The argyrins are secondary metabolites from myxobacteria with antibiotic activity against Pseudomonas aeruginosa. Studying their structure-activity relationship is hampered by the complexity of the chemical total synthesis. Mutasynthesis is a promising approach where simpler and fully synthetic intermediates of the natural product's biosynthesis can be biotechnologically incorporated. Here, we report the synthesis of a series of tripeptide thioesters as mutasynthons containing the native sequence with a dehydroalanine (Dha) Michael acceptor attached to a sarcosine (Sar) and derivatives. Chemical synthesis of the native sequence ᴅ-Ala-Dha-Sar thioester required revision of the sequential peptide synthesis into a convergent strategy where the thioester with sarcosine was formed before coupling to the Dha-containing dipeptide.
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Beilstein J Org Chem. 2019 Dec 5;15:2922-2929. doi: 10.3762/bjoc.15.286. eCollection 2019.
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en
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1860-5397
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Attribution-NonCommercial-ShareAlike 4.0 International